[(Z,2S)-2-[(3S,8S,9S,10R,13S,14S,17S)-3-[tert-butyl(dimethyl)silyl]oxy-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]-6-(1-ethoxyethoxy)-6-methylhept-3-en-2-yl] methyl carbonate | 144042-86-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: [(Z,2S)-2-[(3S,8S,9S,10R,13S,14S,17S)-3-[tert-butyl(dimethyl)silyl]oxy-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]-6-(1-ethoxyethoxy)-6-methylhept-3-en-2-yl] methyl carbonate
• CAS: 144042-86-4
• 化学式: C₃₉H₆₈O₆Si
• 分子量: 661.051
• InChiKey: MJCBCRUBKZGFCL-HMAOPIIESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.62
• 重原子数：
  46
• 可旋转键数：
  14
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  63.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  [(Z,2S)-2-[(3S,8S,9S,10R,13S,14S,17S)-3-[tert-butyl(dimethyl)silyl]oxy-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]-6-(1-ethoxyethoxy)-6-methylhept-3-en-2-yl] methyl carbonate 在 bis(acetylacetonato)palladium(II) 、 三丁基膦 甲酸 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 1.5h， 生成 tert-butyl-[[(3S,8S,9S,10R,13R,14S,17R)-17-[(E,2R)-6-(1-ethoxyethoxy)-6-methylhept-3-en-2-yl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl]oxy]-dimethylsilane
  参考文献：
  名称：

  A novel method for stereospecific generation of either C-20 epimer in steroid side chains by palladium-catalyzed hydrogenolysis of C-20 allylic carbonates

  摘要：

  Both natural and unnatural epimers at C-20 in a steroid side chain can be generated stereospecifically by the palladium-catalyzed hydrogenolysis with triethylammonium formate of C-20 (Z) or (E) allylic carbonates, respectively.

  DOI：

  10.1021/jo00049a004
• 作为产物：
  描述：

  3β-t-butyldimethylsilyloxy-pregn-5-en-20-one 在 正丁基锂 作用下， 生成 [(Z,2S)-2-[(3S,8S,9S,10R,13S,14S,17S)-3-[tert-butyl(dimethyl)silyl]oxy-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]-6-(1-ethoxyethoxy)-6-methylhept-3-en-2-yl] methyl carbonate
  参考文献：
  名称：

  A novel method for stereospecific generation of either C-20 epimer in steroid side chains by palladium-catalyzed hydrogenolysis of C-20 allylic carbonates

  摘要：

  Both natural and unnatural epimers at C-20 in a steroid side chain can be generated stereospecifically by the palladium-catalyzed hydrogenolysis with triethylammonium formate of C-20 (Z) or (E) allylic carbonates, respectively.

  DOI：

  10.1021/jo00049a004

文献信息

• A novel method for stereospecific generation of either C-20 epimer in steroid side chains by palladium-catalyzed hydrogenolysis of C-20 allylic carbonates
  作者：Tadakatsu Mandai、Takaji Matsumoto、Mikio Kawada、Jiro Tsuji

  DOI：10.1021/jo00049a004

  日期：1992.11

  Both natural and unnatural epimers at C-20 in a steroid side chain can be generated stereospecifically by the palladium-catalyzed hydrogenolysis with triethylammonium formate of C-20 (Z) or (E) allylic carbonates, respectively.